My Take: Olivia Palermo (I know, I know...)

I agree, girlfriend needs a total attitude adjustment on "The City".  But, she does dress well and is always perfectly coifed and made up (which of course given her seemingly unlimited funds and time, she darn well should).  So let's just concentrate on the outfit and not the person wearing it - LOL!

I picked this look because it's easy to relate to, I mean I can totally see myself running errands and chasing after my toddler dressed like this.  It's a more pulled together version of yoga pants and grey t-shirt.  I approached it two different ways.  The first way is with the slouchier pants like she's wearing, works better for those of us who don't worry so much about our hips (that would not be me - ha!).  I would love to indulge in these sort of pants, but I'm not sure my borderline pear shape would make them work for me.  Times like this you hit the dressing room hard with lots of options.

Casual Pants by Suoli
Flats by Old Navy

This next option has a more tailored pant keeping the same proportion.  I gave it a slouchier shirt to keep the relaxed feel of the outfit.  Love the bag in this version!

Tees by Forever 21
Flats by Old Navy

Olivia Polermo image via Rikshaw Design blog